5-Exocyclic products, 2,3,5-trisubstituted tetrahydrofurans via prins-type cyclization
- Authors
- Chavre, Satish N.; Choo, Hyunah; Cha, Joo Hwan; Pae, Ae Nim; Choi, Kyung Il; Cho, Yong Seo
- Issue Date
- 2006-08-03
- Publisher
- AMER CHEMICAL SOC
- Citation
- ORGANIC LETTERS, v.8, no.16, pp.3617 - 3619
- Abstract
- 5-Exocyclic products, 2,3,5-trisubstituted tetrahydrofurans, were synthesized from homopropargylic alcohols with terminally substituted alkynes and various aldehydes via Prins-type cyclization. It is of interest that the exocyclic vinyl cation generated as a result of Prins-type cyclization could be trapped as a vinyl triflate when CH2Cl2 was used as a solvent, whereas in ethereal solution the vinyl cation underwent hydrolysis to give the corresponding ketone product.
- Keywords
- STEREOCONTROLLED PREPARATION; ACID; TETRAHYDROPYRAN; EPIMERIZATION; SUPPRESSION; STEREOCONTROLLED PREPARATION; ACID; TETRAHYDROPYRAN; EPIMERIZATION; SUPPRESSION; tetrahydrofuran; 5-exocyclic; prins type cyclization
- ISSN
- 1523-7060
- URI
- https://pubs.kist.re.kr/handle/201004/135247
- DOI
- 10.1021/ol061528x
- Appears in Collections:
- KIST Article > 2006
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